CA1244472A - Process for preparing phenylisopropylurea compounds - Google Patents

Process for preparing phenylisopropylurea compounds

Info

Publication number: CA1244472A
Authority: CA; Canada
Prior art keywords: urea; recited; substituted; phenyl; alkyl
Prior art date: 1984-11-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000495318A

Other languages

English (en)

French (fr)

Inventor

Balwant Singh

Paul S. Waterman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-11-16

Filing date

1985-11-14

Publication date

1988-11-08

1985-11-14 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1988-11-08 Application granted granted Critical

1988-11-08 Publication of CA1244472A publication Critical patent/CA1244472A/en

Status Expired legal-status Critical Current

Links

IHTPIECSQCQMRZ-UHFFFAOYSA-N 1-phenyl-1-propan-2-ylurea Chemical class CC(C)N(C(N)=O)C1=CC=CC=C1 IHTPIECSQCQMRZ-UHFFFAOYSA-N 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 claims abstract description 36
239000004202 carbamide Substances 0.000 claims abstract description 35
-1 alkenyl aromatic compound Chemical class 0.000 claims abstract description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
150000003672 ureas Chemical class 0.000 claims abstract description 21
239000011541 reaction mixture Substances 0.000 claims abstract description 16
239000003377 acid catalyst Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
239000003880 polar aprotic solvent Substances 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical group 0.000 claims abstract description 7
150000002431 hydrogen Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
230000015572 biosynthetic process Effects 0.000 claims abstract description 4
238000003756 stirring Methods 0.000 claims abstract description 3
150000003460 sulfonic acids Chemical class 0.000 claims abstract description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
DMSHKWHLXNDUST-UHFFFAOYSA-N (4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1 DMSHKWHLXNDUST-UHFFFAOYSA-N 0.000 claims description 2
IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 claims description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 claims description 2
229910015900 BF3 Inorganic materials 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
229940000425 combination drug Drugs 0.000 claims 1
229940043265 methyl isobutyl ketone Drugs 0.000 claims 1
239000002841 Lewis acid Chemical class 0.000 abstract description 3
150000007517 lewis acids Chemical class 0.000 abstract description 3
235000013877 carbamide Nutrition 0.000 description 32
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
CYESCLHCWJKRKM-UHFFFAOYSA-N diuron-desdimethyl Chemical compound NC(=O)NC1=CC=C(Cl)C(Cl)=C1 CYESCLHCWJKRKM-UHFFFAOYSA-N 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
XXTQHVKTTBLFRI-UHFFFAOYSA-N m-Isopropenyl toluene Natural products CC(=C)C1=CC=CC(C)=C1 XXTQHVKTTBLFRI-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
OGMSGZZPTQNTIK-UHFFFAOYSA-N o-Isopropenyl toluene Natural products CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-UHFFFAOYSA-N 0.000 description 2
MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
GKEHHLJOYZDXMI-UHFFFAOYSA-N (2,4-dimethylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C(C)=C1 GKEHHLJOYZDXMI-UHFFFAOYSA-N 0.000 description 1
FDKQZWRZKDIMDW-UHFFFAOYSA-N (2-chloro-6-methylphenyl)urea Chemical compound CC1=CC=CC(Cl)=C1NC(N)=O FDKQZWRZKDIMDW-UHFFFAOYSA-N 0.000 description 1
ASPIQYFYSMQBHA-UHFFFAOYSA-N (2-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1Cl ASPIQYFYSMQBHA-UHFFFAOYSA-N 0.000 description 1
WDHPVLQWHRHMEY-UHFFFAOYSA-N (3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(N)=O)=C1 WDHPVLQWHRHMEY-UHFFFAOYSA-N 0.000 description 1
PCKCTBMQZSHNNS-UHFFFAOYSA-N (4-ethylphenyl)urea Chemical compound CCC1=CC=C(NC(N)=O)C=C1 PCKCTBMQZSHNNS-UHFFFAOYSA-N 0.000 description 1
PGUKYDVWVXRPKK-UHFFFAOYSA-N (4-methoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1 PGUKYDVWVXRPKK-UHFFFAOYSA-N 0.000 description 1
WQDGTJOEMPEHHL-UHFFFAOYSA-N 1-chloro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(Cl)C=C1 WQDGTJOEMPEHHL-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
ANZXXZFFQGDFSP-UHFFFAOYSA-N 2-phenylpropan-2-yl thiocyanate Chemical compound N#CSC(C)(C)C1=CC=CC=C1 ANZXXZFFQGDFSP-UHFFFAOYSA-N 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
241001290610 Abildgaardia Species 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
241000219318 Amaranthus Species 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
244000055702 Amaranthus viridis Species 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000722731 Carex Species 0.000 description 1
241000219312 Chenopodium Species 0.000 description 1
235000009344 Chenopodium album Nutrition 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000234653 Cyperus Species 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
244000075634 Cyperus rotundus Species 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
235000017898 Digitaria ciliaris Nutrition 0.000 description 1
235000005476 Digitaria cruciata Nutrition 0.000 description 1
235000006830 Digitaria didactyla Nutrition 0.000 description 1
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
235000012827 Digitaria sp Nutrition 0.000 description 1
241000192043 Echinochloa Species 0.000 description 1
244000058871 Echinochloa crus-galli Species 0.000 description 1
241000202829 Eleocharis Species 0.000 description 1
244000025670 Eleusine indica Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
244000299507 Gossypium hirsutum Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
240000003461 Setaria viridis Species 0.000 description 1
235000002248 Setaria viridis Nutrition 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
244000032225 Stellaria sp Species 0.000 description 1
244000152045 Themeda triandra Species 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
FQEIBEOBXKJAMZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=CC(C(F)(F)F)=C1 FQEIBEOBXKJAMZ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940063656 aluminum chloride Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
244000038559 crop plants Species 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000006182 dimethyl benzyl group Chemical group 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/189—Purification, separation, stabilisation, use of additives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000495318A 1984-11-16 1985-11-14 Process for preparing phenylisopropylurea compounds Expired CA1244472A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/672,038 US4578513A (en)	1984-11-16	1984-11-16	Process for preparing phenylisopropylurea compounds
US672,038		1984-11-16

Publications (1)

Publication Number	Publication Date
CA1244472A true CA1244472A (en)	1988-11-08

Family

ID=24696893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000495318A Expired CA1244472A (en)	1984-11-16	1985-11-14	Process for preparing phenylisopropylurea compounds

Country Status (7)

Country	Link
US (1)	US4578513A (de)
EP (1)	EP0182166B1 (de)
JP (1)	JPS61122262A (de)
KR (1)	KR860004016A (de)
AT (1)	ATE43581T1 (de)
CA (1)	CA1244472A (de)
DE (1)	DE3570657D1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4987248A (en) *	1989-08-02	1991-01-22	E. I. Du Pont De Nemours And Company	Acid catalyzed formation of carbamates from olefins
JP4619511B2 (ja) *	2000-09-29	2011-01-26	Ｏｋｉセミコンダクタ株式会社	電源電圧供給システムを備えた半導体装置及び電源電圧供給システムを備えた半導体装置に電源電圧を供給する電源電圧供給方法
US9421633B2 (en) *	2012-10-09	2016-08-23	Lincoln Global, Inc.	Bulk wire delivery system
MX2019009938A (es) *	2017-03-03	2019-10-09	Dow Global Technologies Llc	Retardante de flama, construcciones de alambres y cables pirorretardantes curados por humedad con rendimiento al impacto tangencial mejorado.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2849485A (en) *	1955-05-11	1958-08-26	Firestone Tire & Rubber Co	Catalytic alkylation of ureas
US3137697A (en) *	1962-03-19	1964-06-16	Shell Oil Co	Tetrahydropyrimidinone production

1984
- 1984-11-16 US US06/672,038 patent/US4578513A/en not_active Expired - Fee Related
1985
- 1985-11-02 AT AT85113939T patent/ATE43581T1/de active
- 1985-11-02 DE DE8585113939T patent/DE3570657D1/de not_active Expired
- 1985-11-02 EP EP85113939A patent/EP0182166B1/de not_active Expired
- 1985-11-14 CA CA000495318A patent/CA1244472A/en not_active Expired
- 1985-11-15 JP JP60255158A patent/JPS61122262A/ja active Pending
- 1985-11-15 KR KR1019850008549A patent/KR860004016A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
DE3570657D1 (en)	1989-07-06
JPS61122262A (ja)	1986-06-10
ATE43581T1 (de)	1989-06-15
US4578513A (en)	1986-03-25
KR860004016A (ko)	1986-06-16
EP0182166A2 (de)	1986-05-28
EP0182166A3 (en)	1987-01-21
EP0182166B1 (de)	1989-05-31

Legal Events

Date	Code	Title	Description
2005-11-14	MKEX	Expiry

Publication	Publication Date	Title
CA1118426A (en)	1982-02-16	Herbicidally active 1,2,4-oxadiazole derivatives, a process for their manufacture and their use
US3935258A (en)	1976-01-27	Process for making N-arylurea compounds and herbicidal compositions containing same
CA1244472A (en)	1988-11-08	Process for preparing phenylisopropylurea compounds
PL187896B1 (pl)	2004-10-29	Sposób wytwarzania pochodnych nitroizomocznika, sposób wytwarzania pochodnych guanidyny i pochodna nitroizomocznika
US4996359A (en)	1991-02-26	Process for the preparation of aromatic bis dialkyl ureas
US4086246A (en)	1978-04-25	Process for the preparation of carbamate derivatives
US4039577A (en)	1977-08-02	Process for preparing phenylisopropylurea derivatives
US3879190A (en)	1975-04-22	Herbicidal allophanimidates
US3962306A (en)	1976-06-08	Sulfonyloxyphenylurea compounds and herbicidal compositions
US3746727A (en)	1973-07-17	Benzenesulfhydroxamic acids and their derivatives
US5525730A (en)	1996-06-11	Processes for preparation of sulfonylurea derivatives
IE48061B1 (en)	1984-09-19	Herbicidally active phenylurea derivatives,a process for their manufacture and their use
US4900827A (en)	1990-02-13	Process for the preparation of pyrimidine derivatives
CA1325810C (en)	1994-01-04	Cyanoacetamido-derivatives having a fungicidal activity
US4348331A (en)	1982-09-07	Process for the preparation of N-substituted imido-dicarboxylic acid diaryl esters
RU2309948C2 (ru)	2007-11-10	Метиловый эфир 4-йод-2-[n-(n-алкиламинокарбонил)аминосульфонил]-бензойной кислоты, его производные и способ их получения
KR100392869B1 (ko)	2003-10-17	4,6-디메톡시-2-((페녹시카르보닐)아미노)-피리미딘의제조방법
GB1572459A (en)	1980-07-30	Herbicidally active urea derivatives process for their manufacture and their use
US4111682A (en)	1978-09-05	N-(aminoalkylene thiomethyl)-N'-(aryl) urea herbicides
US4612385A (en)	1986-09-16	Process for the preparation of phenyl N-(2-biphenylylsulfonyl) carbamate
JPS61183258A (ja)	1986-08-15	置換フエニル尿素の製造方法
US3340254A (en)	1967-09-05	Amino methylene ureas
US4017529A (en)	1977-04-12	Herbicidal allophanimidates
JPH02115167A (ja)	1990-04-27	オキシグアニジンの製造方法
CA1220205A (en)	1987-04-07	Preparation of biphenylylsulfonylureas and intermediates therefor